Gaseous Hydrogen Reactant Patents (Class 568/462)
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Patent number: 10189766Abstract: A process for producing 2-ethylhexanal involves performing reaction using a reaction tank equipped with a gas-introducing mixer having extracting, exhausting, and stirring functions in the presence of a palladium on carbon catalyst having a carbon carrier with lower impurity content and higher specific surface area for hydrogenation, and introducing hydrogen gas evenly into reaction liquid; resulted in that the process minimizes operational pressure for hydrogenation and increases a yield of 2-ethylhexanal at least up to 98.0%.Type: GrantFiled: August 28, 2017Date of Patent: January 29, 2019Assignee: NAN YA PLASTICS CORPORATIONInventors: Te-Chao Liao, Jung-Jen Chuang, Chung-Yu Chen, Chia-Ruey Tsai, Sung-Chieh Chao
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Patent number: 8692028Abstract: Disclosed is a method of hydrogenating an 1,2-unsaturated carbonylic compound to obtain the corresponding saturated carbonylic compound in the presence of a palladium catalyst with heterogeneous distribution of palladium.Type: GrantFiled: December 21, 2010Date of Patent: April 8, 2014Assignee: BioFuel-Solution i Malmo ABInventors: Christian Hulteberg, Jan Brandin
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Patent number: 8389775Abstract: The invention relates to a process for preparing polyether alcohols, which comprises the steps a) reaction of an unsaturated natural oil or fat with a mixture of carbon monoxide and hydrogen, b) reaction of the mixture from step a) with hydrogen, c) reaction of the product from step b) with an alkylene oxide in the presence of a catalyst.Type: GrantFiled: January 26, 2009Date of Patent: March 5, 2013Assignee: BASF SEInventors: Darijo Mijolovic, Andrea Haunert, Andreas Kunst, Stephan Bauer, Qiang Miao, Berend Eling
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Publication number: 20120323043Abstract: Disclosed is a method of hydrogenating an 1,2-unsaturated carbonylic compound to obtain the corresponding saturated carbonylic compound in the presence of a palladium catalyst with heterogeneous distribution of palladium.Type: ApplicationFiled: December 21, 2010Publication date: December 20, 2012Applicant: BioFuel-Solution i Malmo ABInventors: Christian Hulteberg, Jan Brandin
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Publication number: 20080081931Abstract: Disclosed are processes for the preparation of glycolaldehyde in which formaldehyde is contacted with carbon monoxide and hydrogen in the presence of a rhodium catalyst and a solvent containing at least one N,N-dihexylbutyramide. The glycolaldehyde product is recovered by extraction with water. The process provides high selectivity to glycolaldehyde and efficient separation of hydroformylation products from the solvent and rhodium catalyst.Type: ApplicationFiled: September 12, 2007Publication date: April 3, 2008Applicant: EASTMAN CHEMICAL COMPANYInventors: Thomas Allen Puckette, Thomas James Devon
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Publication number: 20070282135Abstract: Process for the catalytic hydrogenation of methylolalkanals of the general formula where R1 and R2 are each, independently of one another, a further methylol group or an alkyl group having from 1 to 22 carbon atoms or an aryl or aralkyl group having from 6 to 33 carbon atoms, in the liquid phase by means of hydrogen over a hydrogenation catalyst, wherein hydrogen is used in a molar ratio to methylolalkanal of greater than 1.Type: ApplicationFiled: June 6, 2006Publication date: December 6, 2007Applicant: BASF AktiengesellschaftInventors: Steffen Maas, Thorsten Johann, Michael Koch, Tilman Sirch, Stephan Schlitter, Stefan Rittinger, Michael Steiniger, Todd C. Spengeman
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Patent number: 7094932Abstract: The present invention provides a method for the production of glycolaldehyde with high specificity. The hydrous thermolysis consists of the spraying of aqueous sugar solutions containing from 25 to 80% of water but preferably 30 to 60% water, as a fine mist into a reactor held at the between 500 and 600° C., but preferably between 520 and 560° C. and the condensation of the resulting vaporous product in a surface condenser with optional heat recovery. The residence time of the vaporous product in the reactor should be in the range 0.1–5 seconds, but preferably in the range 0.5 to 2 seconds. Aldose monomeric sugars, preferably glucose (also known as dextrose), are preferred for use in the aqueous solution. The yield of glycolaldehyde in the condensed liquid is minimum 50% by weight of the sugar fed for glucose solutions.Type: GrantFiled: November 8, 2001Date of Patent: August 22, 2006Assignee: Resource Transforms International Ltd.Inventors: Piotr A. Majerski, Jan K. Piskorz, Desmond St. A. G. Radlein
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Patent number: 6787677Abstract: In a process for the catalytic hydrogenation of a carbonyl compound or a mixture of two or more carbonyl compounds in the presence of catalyst tablets which comprise an inorganic, TiO2-containing support and, as active component, copper or a mixture of copper with at least one metal selected from the group consisting of zinc, aluminum, cerium, nobel metals and metals of transition group VIII and whose copper surface area is not more than 10 m2/g, the diameter d and/or the height h of the tablets is less than 3 mm.Type: GrantFiled: September 29, 2003Date of Patent: September 7, 2004Assignee: BASF AktiengesellschaftInventors: Michael Koch, Steffen Maas, Wolfgang Jürgen Pöpel, Matthias Dernbach
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Patent number: 6369277Abstract: An &agr;,&bgr;-unsaturated carbonyl compound of formula (I) where R1 is saturated C1-40-hydrocarbyl or a substituted or unsubstituted aromatic radical containing moiety, and R2, R3 and R4, independently of one another, are hydrogen or a C1- to C4-alkyl group, is selectively hydrogenated in the liquid phase to a saturated carbonyl compound of formula (II) with hydrogen in the presence of a pulverulent palladium and/or rhodium catalyst and in the presence of an organic base, by conducting the hydrogenation in a packed bubble column reactor in which product is recycled and hydrogen gas is recirculated.Type: GrantFiled: August 25, 2000Date of Patent: April 9, 2002Assignee: BASF AktiengesellschaftInventors: Franz Josef Broecker, Gerd Kaibel, Werner Aquila, Hartwig Fuchs, Guenter Wegner, Manfred Stroezel
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Patent number: 6340778Abstract: The invention relates to a process for the catalytic aldol condensation of aldehydes by means of a multiphase reaction in a tube reactor, wherein the catalyst is present in the continuous phase and at least one aldehyde is present in a dispersed phase and the loading factor B of the tube reactor is equal to or greater than 0.8; the aldol condensation products obtained in this way can be used for preparing alcohols or carboxylic acids.Type: GrantFiled: October 24, 2000Date of Patent: January 22, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann, Juergen Koch
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Patent number: 6150564Abstract: The invention relates to a process for the selective liquid-phase hydrogenation of .alpha.,.beta.-unsaturated carbonyl compounds of the formula I, ##STR1## where R.sub.1 is hydrogen or an organic radical, and R.sub.2, R.sub.3 and R.sub.4, independently of one another, are hydrogen or a C.sub.1 -- to C.sub.4 --alkyl group, to saturated carbonyl compounds of the formula II ##STR2## using hydrogen in the presence of a pulverulent palladium and/or rhodium catalyst and in the presence of an organic base. The process is carried out in a packed bubble column reactor (1, 2) with product recycling (11, 17) and circulating hydrogen gas (4, 15, 16). It is particularly suitable for the selective hydrogenation of citral to citronellal.Type: GrantFiled: March 25, 1999Date of Patent: November 21, 2000Assignee: BASF AktiengesellschaftInventors: Franz Josef Brocker, Gerd Kaibel, Werner Aquila, Hartwig Fuchs, Gunter Wegner, Manfred Stroezel
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Patent number: 6114588Abstract: A method to produce dialcohols is provided, the method comprising the steps of:providing a feed stream comprising an alpha-alcohol-diolefin;reacting the feed stream with hydrogen and carbon monoxide in the presence of a catalyst system comprising a cobalt phosphine ligand complex under conditions effective to hydroformylate at least a portion of the diolefin in the feed stream; andrecovering the dialcohol from the reacted feed stream. This method is a one-step process to hydroformylate alpha-alcohol-diolefins such as 2,7-octadien-1-ol to produce a significant yield of dialcohols such as 1,9-nonanediol.Type: GrantFiled: June 11, 1998Date of Patent: September 5, 2000Assignee: Shell Oil CompanyInventors: Pui-Kwan Wong, Andrew Allison Moxey
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Patent number: 5756856Abstract: The present invention relates to a process for the preparation of 2-ethylhexanal by catalytic hydrogenation of 2-ethylhex-2-enal, wherein the hydrogenation is carried out in a plurality of two or more series-connected loops, wherein each loop involves the use of one reactor, which comprises:(a) feeding 2-ethylhex-2-enal and hydrogen to an upper part of a reactor to catalytically hydrogenate said 2-ethylhex-2-enal to produce a hydrogenation product,(b) recycling a portion of said hydrogenation product back into said upper part of said reactor,(c) feeding the remainder of said hydrogenation product from said reactor to an upper part of a subsequent reactor wherein 2-ethylhex-2-enal is catalytically hydrogenated to produce a subsequent hydrogenation product, and wherein a portion of said subsequent hydrogenation product has been recycled and is fed with said remainder of said hydrogenation product to said upper part of said subsequent reactor,(d) repeating step (c) until the subsequent reactor is the last reactoType: GrantFiled: June 26, 1996Date of Patent: May 26, 1998Assignee: Huels AktiengesellschaftInventors: Wilfried Bueschken, Juergen Hummel
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Patent number: 5650546Abstract: A process for the hydrogenation of organic compounds using water soluble catalyst in a biphasic media by: (A) forming an organo-water dispersion of (i) an organic phase having (a) an organic compound and (b) an organic solvent, and (ii) an aqueous phase having a water soluble group VIII metal catalyst composition and a water soluble ligand; and (B) contacting said dispersion with hydrogen to provide an interfacial reaction between said organic compound and said hydrogen, giving significant enhancement in the rate of reaction to produce saturated organic compound as compared to a reaction carried out in the absence of said water immiscible ligand.Type: GrantFiled: December 16, 1994Date of Patent: July 22, 1997Assignee: Council of Scientific Industrial Resear.Inventors: Raghunath Vitthal Chaudhari, Bhalchandra Mahadeo Bhanage, Sunil Sadashiv Divekar, Raj Madhukar Deshpande
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Patent number: 5254743Abstract: Solid solutions of a class of divalent metal oxides and a class of trivalent metal oxides resulting from calcination of layered double hydroxides related to hydrotalcite have been prepared with a surface area in excess of 150 m.sup.2 /g. Such high surface area materials are found to be quite effective in the aldol condensation of aldehydes and ketones, and in particular in the conversion of n-butyraldehyde to 2-ethyl-2-hexenal in high yield and with good selectivity in a liquid phase reaction at temperatures under about 200.degree. C. Variants can be devised where the aldol condensation product, an .alpha.,.beta.-unsaturated aldehyde or ketone, is concurrently reduced to the saturated alcohol under process conditions.Type: GrantFiled: December 9, 1992Date of Patent: October 19, 1993Assignee: UOPInventors: Jennifer S. Holmgren, Blaise J. Arena
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Patent number: 5235118Abstract: Disclosed is a continuous process for the manufacture of 2-ethyl-2-(hydroxymethyl)hexanal wherein 2-ethylhexanal, formaldehyde and a tertiary amine are continuously fed to a reaction zone and crude product comprising an aqueous phase and an organic phase containing 2-ethyl-2-(hydroxymethyl)hexanal and 2-ethylhexanal is continuously removed from the reaction zone Also disclosed are processes for (1) the azeotropic distillation of the organic phase of the crude product whereby unreacted 2-ethylhexanal is recovered and (2) the catalytic hydrogenation of the refined, organic phase of the crude product to produce 2-butyl-2-ethyl-1,3-propanediol.Type: GrantFiled: August 31, 1992Date of Patent: August 10, 1993Assignee: Eastman Kodak CompanyInventors: Don L. Morris, William A. Beavers, William E. Choate
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Patent number: 5026919Abstract: Basic intermediate or large pore zeolites having a Constraint Index less than 12 are useful as catalysts in the dehydrogenation-aromatization of cyclie dienes, in the isomerization of olefins and in the aldol condensation, and particularly in the cyclization of acetonylacetone to 3-methyl-2-cyclopenten-1-one.Type: GrantFiled: December 20, 1985Date of Patent: June 25, 1991Assignee: Mobil Oil CorporationInventor: Ralph M. Dessau
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Patent number: 5015780Abstract: Dihalobutyraldehydes of formula I ##STR1## wherein X and Y are each independently of the other Cl or Br, are obtainable at high rates of conversion and with excellent selectivities by catalytic dehalogenation with hydrogen by carrying out the reaction with appropriate .alpha.,.alpha.-dihalobutyraldehydes in an organic aprotic solvent. The dihalobutyraldehydes are intermediates for the synthesis of herbicidal acyl cyclohexanediones.Type: GrantFiled: January 16, 1990Date of Patent: May 14, 1991Assignee: Ciba-Geigy CorporationInventors: Heinz Steiner, Hans Tobler
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Patent number: 5003110Abstract: Saturated aldehydes are prepared by hydrogenation of .alpha.,.beta.-unsaturated aldehydes in a two-phase medium in the presence of a catalyst consisting of a rhodium derivative combined with a water-soluble ligand or of a rhodium complex with a water-soluble ligand.Type: GrantFiled: September 25, 1989Date of Patent: March 26, 1991Assignee: Rhone-Poulenc SanteInventor: Jean-Michel Grosselin
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Patent number: 4847423Abstract: Aqueous formaldehyde is hydroformylated to glycol aldehyde in the presence of a rhodium-phosphine ligand complex catalyst in which the phosphine ligand is a trialkyl- or tricycloalkylphosphine and has a specified cone angle. A preferred phosphine ligand is tricyclohexylphosphine.Type: GrantFiled: March 3, 1988Date of Patent: July 11, 1989Assignee: Hoechst Celanese CorporationInventors: Robert J. Koprowski, Jerry D. Unruh
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Patent number: 4701562Abstract: Aldehydes can be condensed with ketones or aldehydes to produce higher aldehydes or ketones by contacting the materials to be condensed with a nonzeolitic molecular sieve. The condensation may be carried out in the presence of hydrogen to give as product a saturated aldehyde or ketone. The ketone and/or aldehyde may be generated in situ by dehydrogenation of an alcohol, and the hydrogen thus liberated used to effect hydrogenation of the immediate unsaturated product of the condensation, thereby producing as the final product a saturated aldehyde or ketone. The non-zeolitic molecular sieves can achieve improved conversion rates and selectivities as compared with conventional catalysts for the reaction.Type: GrantFiled: June 25, 1986Date of Patent: October 20, 1987Assignee: Union Carbide CorporationInventor: Kurt D. Olson
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Patent number: 4677230Abstract: 2-Methyl-2-alkenals of the formula ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, alkyl which may additionally carry aromatic radicals, or an aromatic radical, are prepared by isomerizing a 2-alkylacrolein of the formula ##STR2## in the presence of hydrogen and of a catalyst which contains palladium and an oxide or salt of a rare earth metal as active components, at from 20.degree. to 120.degree. C. and under from 1 to 100 bar.Type: GrantFiled: June 11, 1986Date of Patent: June 30, 1987Assignee: BASF AktiengesellschaftInventors: Leopold Hupfer, Franz Merger, Franz J. Broecker, Rolf Fischer
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Patent number: 4608444Abstract: A process and accompanying catalyst for the hydroformylation of formaldehyde to glycol aldehyde is disclosed. The process features the utilization of (1) a class of transition metal phosphine-amide complexes, (2) a class of transition metal phosphine-amine complexes, and (3) mixtures of 1 and 2 as particularly suitable for use.Type: GrantFiled: March 1, 1985Date of Patent: August 26, 1986Assignee: The Halcon SD Group, Inc.Inventor: Stephen E. Jacobson
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Patent number: 4605797Abstract: Selective hydrogenation process is provided employing as catalyst a composition consisting essentially of elemental palladium on calcium carbonate support with lead acetate and an aromatic amine oxide. Very high selectivities to cis-olefinic compounds from acetylenic compounds is achieved employing the catalyst of the invention.Type: GrantFiled: December 20, 1984Date of Patent: August 12, 1986Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: 4599469Abstract: Process for the hydrogenation of functionally substituted acetylenic compounds employing catalyst comprising nickel boride on an inorganic oxide support is disclosed. Functionally-substituted acetylenic compounds are selectively reduced under mild reaction conditions to give functionally-substituted cis-olefinic compounds in high yield.Type: GrantFiled: May 29, 1984Date of Patent: July 8, 1986Assignee: Phillips Petroleum CompanyInventors: Ted H. Cymbaluk, Jim D. Byers, Marvin M. Johnson
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Patent number: 4590298Abstract: This invention provides a process for the production of C.sub.4 -C.sub.5 hydroxyketones by reaction of formaldehyde and synthesis gas in a basic organic solvent in the presence of a tungsten and Group VIII metal-containing catalyst composition.Type: GrantFiled: March 5, 1985Date of Patent: May 20, 1986Assignee: Celanese CorporationInventor: Tessie M. Che
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Patent number: 4560806Abstract: An improved transition metal-phosphine-amide hydroformylation catalyst is disclosed having a substantially increased solubility in non-polar organic solvents, thereby preventing migration of the catalyst into the glycol aldehyde product during the hydroformylation process and subsequent separation operations, greatly facilitating and improving the catalyst separation and recycle operations.Type: GrantFiled: April 5, 1984Date of Patent: December 24, 1985Assignee: The Halcon SD Group, Inc.Inventor: Stephen E. Jacobson
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Patent number: 4503260Abstract: Hemi-formals are reacted with hydrogen and carbon monoxide in the presence of certain rhodium catalysts to form glycol aldehyde.Type: GrantFiled: June 13, 1983Date of Patent: March 5, 1985Assignee: Monsanto CompanyInventors: Steven R. Auvil, Patrick L. Mills
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Patent number: 4496781Abstract: A process for the preparation and purification of a glycol aldehyde intermediate which is later hydrogenated to ethylene glycol is disclosed. The process proceeds via the catalytic reaction of formaldehyde, carbon monoxide and hydrogen and utilizes a novel class of lipophilic rhodium phosphine amide catalysts and an effective solvent mixture, which enables efficient catalyst separation and recycle without the loss of a substantial amount of the expensive catalyst.Type: GrantFiled: April 5, 1984Date of Patent: January 29, 1985Assignee: The Halcon SD Group, Inc.Inventors: Stephen E. Jacobson, Chun F. Chueh
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Patent number: 4477685Abstract: Formaldehyde is reacted with hydrogen and carbon monoxide with rhodium catalyst in the presence of phosphine ligands having electron-withdrawing substituents, obtaining high selectivity to glycol aldehyde with a stable catalyst system.Type: GrantFiled: August 20, 1982Date of Patent: October 16, 1984Assignee: Monsanto CompanyInventor: Albert S. Chan
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Patent number: 4450300Abstract: For the continuous manufacture of n-butyraldehyde by selective hydrogenation of crotonaldehyde, the hydrogenation is conducted in the liquid phase in the presence of a palladium-aluminum oxide supported catalyst containing the palladium in the outer layer of the supporting grain of a thickness of 0.05-0.2 mm. The palladium content of this catalyst is 0.1-0.6% by weight. The aluminum oxide support, with a specific pore volume of 0.4-0.6 cm.sup.3 /g, has 40-60% of its pores of a diameter of >0.5 nm and an internal surface area of 130-160 m.sup.2 /g. The hydrogenation is conducted under absolute pressures of 5-50 bar and at temperatures of 20.degree.-100.degree. C. The resultant n-butyraldehyde is of a high purity without interfering by-products.Type: GrantFiled: March 12, 1982Date of Patent: May 22, 1984Assignee: Chemische Werke Huels AktiengesellschaftInventors: Lothar Fischer, Manfred Z. Hausen, Kurt Wember
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Patent number: 4429165Abstract: Process for selective production of acetaldehyde and dimethyl acetal by the reaction of methanol with carbon monoxide in contact with a catalyst containing cobalt atom, halide atom and a mixture of a trivalent phosphorus compound and a trivalent nitrogen compound. The amount of trivalent nitrogen compound in its mixture varies from 5 mole percent to 50 mole percent of such mixture.Type: GrantFiled: June 24, 1982Date of Patent: January 31, 1984Assignee: Union Carbide CorporationInventor: Richard W. Wegman
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Patent number: 4420648Abstract: Supported coprecipitated cobalt-silica hydrogenation catalysts are disclosed. The catalysts are prepared by: preparing an aqueous reaction mixture containing cobalt cations, silicate anions and solid porous carrier particles under agitation to form a coprecipitate of the cobalt and silicate ions onto said solid porous support particles; heating the aqueous reaction mixture; and adding an alkaline precipitating agent to further precipitate the cobalt and silicate ions onto said solid porous carrier particles. The aqueous reaction mixture may additionally include copper cations.Type: GrantFiled: September 19, 1979Date of Patent: December 13, 1983Assignee: Exxon Research and Engineering Co.Inventors: James L. Carter, Allan E. Barnett
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Patent number: 4414421Abstract: A process for the preparation of glycol aldehyde, which comprises reacting formaldehyde with hydrogen and carbon monoxide, in the presence of a rhodium- and/or a cobalt-containing catalyst, sulphur dioxide, and water.Type: GrantFiled: May 26, 1982Date of Patent: November 8, 1983Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4405821Abstract: In the process for producing glycolaldehyde and/or ethylene glycol by the reaction of formaldehyde, carbon monoxide and hydrogen in a non-amide solvent at elevated temperature and superatmospheric pressure in the presence of a catalytic amount of a rhodium-containing catalyst, an improvement is provided which comprises carrying out said reaction in the presence of a glycolaldehyde yield-enhancing phosphine oxide.Type: GrantFiled: August 11, 1981Date of Patent: September 20, 1983Assignee: National Distillers and Chemical CorporationInventor: Richard W. Goetz
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Patent number: 4405814Abstract: Formaldehyde is reacted with hydrogen and carbon monoxide in the presence of certain rhodium catalysts and basic organic amine compositions which promote the formation of glycol aldehyde.Type: GrantFiled: August 5, 1981Date of Patent: September 20, 1983Assignee: Monsanto CompanyInventors: W. Eamon Carroll, Albert S. Chan
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Patent number: 4394525Abstract: A process for hydrogenating an unsaturated organic compound which comprises contacting the same with hydrogen in the presence of a catalyst composed of a support containing (1) at least one Group IIA metal compound selected from the group consisting of magnesium, calcium, strontium and barium compounds, (2) alumina and (3) aluminum phosphate carrying nickel thereon.Type: GrantFiled: June 29, 1981Date of Patent: July 19, 1983Assignee: Gulf Research & Development CompanyInventors: Roger F. Vogel, George Marcelin, Harold E. Swift
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Patent number: 4382148Abstract: A process for the preparation of glycol aldehyde, which comprises reacting formaldehyde with hydrogen and carbon monoxide, in the presence of a catalyst system derived from a rhodium-containing catalyst precursor and/or a cobalt-containing catalyst precursor together with a strong protonic acid.Type: GrantFiled: October 27, 1981Date of Patent: May 3, 1983Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4365095Abstract: A process for hydrogenating an unsaturated organic compound which comprises contacting the same with hydrogen in the presence of a catalyst composed of a support containing (1) (A) a Group IIB metal compound selected from the group consisting of zinc and cadmium compounds, (B) a combination of said zinc and cadmium compounds or (C) a combination of at least one of said Group IIB metal compounds with at least one Group IIA metal compound selected from the group consisting of magnesium, calcium, strontium and barium compounds, (2) alumina and (3) aluminum phosphate and carrying nickel thereon.Type: GrantFiled: August 3, 1981Date of Patent: December 21, 1982Assignee: Gulf Research & Development CompanyInventors: George Marcelin, Roger F. Vogel, Harold E. Swift
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Patent number: 4361705Abstract: A process for hydrogenating an unsaturated organic compound which comprises contacting the same with hydrogen in the presence of a catalyst composed of a support containing alumina and aluminum phosphate carrying nickel thereon.Type: GrantFiled: June 29, 1981Date of Patent: November 30, 1982Assignee: Gulf Research & Development CompanyInventors: George Marcelin, Roger F. Vogel, Harold E. Swift
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Patent number: 4317925Abstract: A process for the preparation of di-n-propylacetic acid which comprises the steps ofA. converting n-valeraldehyde-diallyl acetal into allyl-1-pentenyl ether by cleaving one mol of allyl alcohol per one mol of n-valeraldehye-diallyl acetal;B. rearranging the allyl-1-pentenyl ether thermally into 2-propyl-pent-4-en-1-al,C. partially hydrogenating the 2-propyl-pent-en-1-al catalytically to form 2-propyl valeraldehyde, andD. oxidizing the 2-propyl valeraldehyde to form dipropyl-acetic acid.Type: GrantFiled: July 25, 1979Date of Patent: March 2, 1982Assignee: Ruhrchemie AktiengesellschaftInventors: Jurgen Weber, Wolfgang Bernhagen, Helmut Springer
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Patent number: 4317945Abstract: A process for the preparation of 2-methyl-2-sec.butyl-1,3-propanediol comprising hydroformylating 2-methyl-1-butene with carbon monoxide and hydrogen in the presence of a first catalyst to form the substance 3-methyl-pentanal, condensing said substance with formaldehyde, or a compound which forms formaldehyde under the conditions of condensation in a basic medium to form alpha-sec.butyl-acrolein, partially hydrogenating said acrolein in the presence of a second catalyst to form the material 2,3-dimethyl pentanal, and converting said material into said diol by treatment with formaldehyde, or a compound which forms formaldehyde under the conditions of conversion, in the presence of a strong base as a third catalyst.The compound of the present invention is useful as an intermediate in the production of pharmaceuticals and drugs; in particular, the production of carbamates which are useful as tranquilizers and blood pressure lowering agents.Type: GrantFiled: August 15, 1980Date of Patent: March 2, 1982Assignee: Ruhrchemie AktiengesellschaftInventors: Wolfgang Bernhagen, Jurgen Weber, Helmut Bahrmann, Helmut Springer
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Patent number: 4291179Abstract: Acetaldehyde and ethanol are produced by the catalyzed reaction of formaldehyde, carbon monoxide and hydrogen using a halogen-containing rhodium catalyst.Type: GrantFiled: April 21, 1980Date of Patent: September 22, 1981Assignee: National Distillers and Chemical Corp.Inventors: Richard W. Goetz, Lawrence D. Meixsel, David W. Smith
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Patent number: 4273945Abstract: Saturated aliphatic, cycloaliphatic and araliphatic aldehydes are prepared by selective hydrogenation of the corresponding olefinically unsaturated aldehydes with hydrogen in the liquid phase over a palladium-containing catalyst, using a catalyst system in which the active constituents are from 2 to 90% by weight of palladium and from 10 to 98% by weight of an oxide or a salt of a rare earth metal or of a mixture of different oxides and/or salts of this type.Type: GrantFiled: July 5, 1979Date of Patent: June 16, 1981Assignee: BASF AktiengesellschaftInventors: Gerd Heilen, Axel Nissen, Wolfgang Koernig, Michael Horner, Werner Fliege, Guenter Boettger
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Patent number: 4270006Abstract: Aliphatic carbonyl compounds are prepared by an aldol condensation of carbonyl compounds R.sup.1 --CH.sub.2 --CO--R.sup.2 (I; R.sup.1 and R.sup.2 =H or C.sub.1 -C.sub.8 -alkyl) in the presence of hydrogen and of a catalyst which has both condensing and hydrogenating properties, by using a catalyst system wherein the active components are from 1 to 90 percent by weight of a noble metal of group VIII of the periodic table and from 10 to 99 percent by weight of an oxide or salt of a rare earth metal, or of a mixture of different oxides and/or salts of rare earth metals.Type: GrantFiled: December 27, 1979Date of Patent: May 26, 1981Assignee: BASF AktiengesellschaftInventors: Gerd Heilen, Axel Nissen, Otto Woerz
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Patent number: 4267384Abstract: Acetaldehyde and ethanol are produced by the reaction of formaldehyde, carbon monoxide and hydrogen using a halogen-containing ruthenium catalyst.Type: GrantFiled: April 21, 1980Date of Patent: May 12, 1981Assignee: National Distillers and Chemical Corp.Inventor: David W. Smith
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Patent number: 4263225Abstract: Supported coprecipitated nickel-cobalt-silica and nickel-cobalt-copper-silica hydrogenation catalysts are disclosed. The catalysts are prepared by preparing an aqueous reaction mixture containing nickel and cobalt cations (and optionally copper cations), silicate anions and solid porous carrier particles under agitation to form a coprecipitate of the nickel, cobalt (and optionally copper) and silicate ions onto said solid porous support particles; heating the aqueous reaction mixture; and adding an alkaline precipitating agent to further precipitate the nickel, cobalt (and optionally copper) and silicate anions onto said solid porous carrier particles.Type: GrantFiled: September 19, 1979Date of Patent: April 21, 1981Assignee: Exxon Research & Engineering Co.Inventors: James L. Carter, Allan E. Barnett, John H. Sinfelt
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Patent number: 4260829Abstract: Carbonyl compounds R.sup.1 --CHR.sup.2 --CHR.sup.3 --CR.sup.4 O (I, R.sup.1 =H or an organic radical; R.sup.2 -R.sup.4 =H or C.sub.1 -C.sub.4 -alkyl) are prepared by selective hydrogenation of the .alpha.,.beta.-unsaturated carbonyl compounds R.sup.1 --CR.sup.2 =CR.sup.3 --CR.sup.4 O (II) in the liquid phase by means of hydrogen in the presence of a palladium catalyst and of from 15 to 50% by weight, based on (II), of a tertiary amine.Type: GrantFiled: August 17, 1979Date of Patent: April 7, 1981Assignee: BASF AktiengesellschaftInventors: Michael Horner, Axel Nissen, Peter R. Laurer, Matthias Irgang, Heinrich Pasedach
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Patent number: RE32084Abstract: A process for preparing glycol aldehyde by reacting formaldehyde, hydrogen and carbon monoxide at elevated temperature and superatmospheric pressure in the presence of rhodium catalyst and conversion thereof to ethylene glycol as the substantially exclusive polyol product.Type: GrantFiled: October 4, 1983Date of Patent: February 18, 1986Assignee: National Distillers and Chemical CorporationInventor: Richard Goetz